تفاعل #40594

معادلة التفاعل

8a

(2S,4aS,6aR,7R,9S,10aS,10bR)-9-(hydroxy)-2-(3-furanyl)dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester

methanesulfonyl chloride

NEt3

→

white solid

المردود 32.0%

(2S,4aR,6aR,7R,9S,10aS,10bR)-9-(methanesulfonyloxy)-2-(3-furanyl)-dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester

المردود 32.0%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   غسيلthe mixture was washed with saturated NaHCO3 (20 mL) and saturated NaCl (2×15 mL)
2. 2
   تجفيفdried (Na2SO4)
3. 3
   أخرىThe solvent was removed under reduced pressure
4. 4
   أخرىThe resulting crude solid was purified by column chromatography (eluent: ethyl acetate/n-hexanes)

الإجراء التجريبي

A solution of 8a (0.05 g, 0.13 mmol), methanesulfonyl chloride (1 mL) and NEt3 (2 mL) in CH2Cl2 (30 mL) was stirred at room temperature overnight and then the mixture was washed with saturated NaHCO3 (20 mL) and saturated NaCl (2×15 mL) and dried (Na2SO4). The solvent was removed under reduced pressure. The resulting crude solid was purified by column chromatography (eluent: ethyl acetate/n-hexanes) to afford 0.02 g (32%) of a white solid, mp 147-150° C.; 1H NMR (CDCl3): δ 1.14 (3H, s, H-19); 1.47 (3H, s, H-20); 1.50-1.70 (3H, m, H-7α,β and H-11β); 1.81 (1H, m, H-6α); 2.11 (1H, dd, J=2.9, 11.3 Hz, H-8); 2.16 (1H, s, H-10); 2.19 (1H, m, H-6β); 2.42 (1H, dd, J=13.2, 13.2 Hz, H-3α); 2.50 (1H, m, H-3β); 2.52 (1H, dd, J=4.8, 13.2 Hz, H-11α); 2.75 (1H, dd, J=3.6, 13.2 Hz, H-4); 3.25 (3H, s, CH3SO2); 3.74 (3H, s, CO2CH3); 5.07 (1H, dd, J=8.0, 12.2 Hz, H-2); 5.55 (1H, dd, J=5.1, 11.7 Hz, H-12); 6.41 (1H, dd, J=0.9, 1.8 Hz, H-14); 7.42 (1H, dd, J=1.8, 1.8 Hz, H-15); 7.45 (1H, br d).

المصدر